Adenosine monophosphate
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| Adenosine monophosphate | |
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| Chemical name | 5'-Adenylic acid |
| Chemical formula | C10H14N5O7P |
| Molecular mass | 347.22 g/mol |
| CAS number | 61-19-8 |
| SMILES | O[C@H]1[C@H]([C@@H](O[C@@H]1COP(O)(O)=O)N2C3=C(N=C2)C(N)=NC=N3)O |
| Missing image AMP_chemical_structure.png Chemical structure of deprotonated AMP | |
Adenosine monophosphate, also known as 5'-adenylic acid and abbreviated AMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside adenosine. AMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase adenine.
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Production and degradation
AMP can be produced during ATP synthesis by the enzyme adenylate kinase by combining two ADP molecules:
- 2 ADP → ATP + AMP
Or AMP may be produced by the hydrolysis of one high energy phosphate bond of ADP:
- ADP → AMP + Pi
AMP can also be formed by hydrolysis of ATP into AMP and pyrophosphate:
- ATP → AMP + PPi
When RNA is broken down by living systems, nucleoside monophosphates, including adenosine monophosphate, are formed.
AMP can be regenerated to ATP as follows:
- AMP + ATP → 2 ADP (adenylate kinase in the opposite direction)
- 2 ADP + 2 Pi → 2 ATP (this step is most often performed in aerobes by the ATP synthase during oxidative phosphorylation)
AMP can be converted into IMP by the enzyme myoadenylate deaminase, freeing an ammonia group.
In a catabolic pathway, adenosine monophosphate can be converted to uric acid, which is excreted from the body.
cAMP
AMP can also exist as a cyclic structure known as cyclic AMP (or cAMP). Within certain cells the enzyme adenylate cyclase makes cAMP from ATP, and typically this reaction is regulated by hormones such as adrenaline or glucagon. cAMP plays an important role in intracellular signalling.
Commercial applications
Linguagen Corp obtained FDA approval in September 2004 to employ AMP as a patented 'Bitter Blocker' additive to foodstuffs. To human tastes, the bitterness suppressing quality of AMP interprets as food seeming 'sweeter'. This makes lower calorie food products more palatable, making AMP potentially a lucrative solution for food manufacturers as they respond to pressure from consumers and regulators concerned about social trends towards obesity.